Organic Chemistry / Edition 6

Organic Chemistry / Edition 6

by Francis A. Carey

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ISBN-10: 0072966882

ISBN-13: 9780072966886

Pub. Date: 01/28/2005

Publisher: McGraw-Hill Companies, The

A Market Leading, Traditional Approach to Organic Chemistry

Throughout all seven editions, Organic Chemistry has been designed to meet the needs of the "mainstream," two-semester, undergraduate organic chemistry course. This best-selling text gives students a solid understanding of organic chemistry by stressing how fundamental reaction


A Market Leading, Traditional Approach to Organic Chemistry

Throughout all seven editions, Organic Chemistry has been designed to meet the needs of the "mainstream," two-semester, undergraduate organic chemistry course. This best-selling text gives students a solid understanding of organic chemistry by stressing how fundamental reaction mechanisms function and reactions occur. With the addition of handwritten solutions, new cutting-edge molecular illustrations, updated spectroscopy coverage, seamless integration of molecular modeling exercises, and state-of-the-art multimedia tools, the 7th edition of Organic Chemistry clearly offers the most up-to-date approach to the study of organic chemistry.

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McGraw-Hill Companies, The
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New Edition
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Table of Contents

Chapter 1 - Structure Determines Properties
1.1 Atoms, Electrons, and Orbitals
1.2 Ionic Bonds
1.3 Covalent Bonds, Lewis Structures, and the Ocelet Rule
1.4 Double Bonds and Triple Bonds
1.5 Polar Covalent Bonds and Electronegativity
Electrostatic Potential Maps
1.6 Structural Formuala of Organic Molecules
1.7 Formal Charge
1.8 Resonance
1.9 The Shape of Some Simple Molecules
Molecular Modeling
1.10 Molecular Dipole Moments
1.11 Curved Arrows and Chemical Reactions
1.12 Acids and Bases: The Arrhenius View
1.13 Acids and Bases: The Brønsted-Lowry View
1.14 What Happened to pKb?
1.15 How Structure Affects Acid Strength
1.16 Acid-Base Equilibria
1.17 Lewis Acids and Lewis Bases
1.18 Summary
Descriptive Passage and Interpretive Problems 1: Amide Lewis Structures.
Chapter 2 - Alkanes and Cycloakanes: Introduction to Hydrocarbons
2.1 Classes of Hydrocarbons
2.2 Electron Waves and Chemical Bonds
2.3 Bonding in H2: The Valence Bond Model
2.4 Bonding in H2: The Molecular Orbital Model
2.5 Introduction to Alkanes: Methane, Ethane, and Propane
Methane and the Biosphere
2.6 sp3 Hybridization and Bonding in Methane
2.7 Bonding in Ethane
2.8 Isomeric Alkanes: The Butanes
2.9 Higher n -Alkanes
2.10 The C5H12 Isomers
2.11 IUPAC Nomenclature of Unbranched Alkanes
What's in a Name? Organic Nonmenclature
2.12 Applying the IUPAC Rules: The Names of the C6H14 Isomers
2.13 Alkyl Groups
2.14 IUPAC Names of Highly Branched Alkanes
2.15 Cycloalkane Nomenclature
2.16 Sources of Alkanes andCycloalkanes
2.17 Physical Properties of Alkanes and Cycloalkanes
2.18 Chemical Properties. Combustion of Alkanes
2.19 Oxidation-Reduction in Organic Chemistry
2.20 sp2 Hybridization and Bonding in Ethylene
2.21 sp Hybridization and Bonding in Acetylene
2.22 Which Theory of Chemical Bonding is Best?
2.23 Summary
Descriptive Passage and Interpretive Problems 2: Some Biochemical Reactions of Alkanes
Chapter 3 - Alkanes andCycloalkanes: Conformations and cis-trans Stereoisomers
3.1 Conformational Analysis of Ethane
3.2 Conformational Analysis of Butane
Molecular Mechanics Applied to Alkanes and Cycloalkanes
3.3 Conformations of Higher Alkanes
3.4 The Shapes of Cycloalkanes: Planar or Nonplanar
3.5 Small Rings: Cyclopropane and Cyclobutane
3.6 Cyclopentane
3.7 Conformations of Cyclohexane
3.8 Axial and Equatorial Bonds in Cyclohexane
3.9 Conformational Inversion (Ring Flipping) in Cyclohexane
3.10 Conformational Analysis of Monosubstituted Cyclohexanes
3.11 Disubstituted Cycloalkanes. Stereoisomers
Enthalpy, Free Energy, and Equilibrium Constant
3.12 Conformational Analysis of Disubstituted Cyclohexanes
3.13 Medium and Large Rings
3.14 Polycyclic Ring Systems
3.15 Heterocyclic Compounds
3.16 Summary
Descriptive Passage and Interpretive Problems 3: Cylic Forms of Carbohydrates
Chapter 4 - Alcohols and Alkyl Halides
4.1 Functional Groups
4.2 IUPAC Nomenclature of Alkyl Halides
4.3 IUPAC Nomenclature of Alcohols
4.4 Classes of Alcohols and Alkyl Halides
4.5 Bonding in Alcohols and Alkyl Halides
4.6 Physical Properties of Alcohols and Alkyl Halides: Intermolecular Forces
4.7 Preparation of Alkyl Halides From Alcohols and Hydrogen Halides
4.8 Mechanism of the Reaction of Alcohols with Hydrogen Halides
4.9 Potential Energy Diagrams for Multistep Reactions. The SN1 Mechanism
4.10 Structure, Bonding, and Stability of Carbocations
4.11 Effect of Alcohol Structure on Reaction Rate
4.12 Reaction of Primary Alcohols with Hydrogen Halides. The SN2 Mechanism
4.13 Other Methods for Converting Alcohols to Alkyl Halides
4.14 Halogenation of Alkanes
4.15 Chlorination of Methane
4.16 Structure and Stability of Free Radicals
4.17 Mechanism of Methane Chlorination
4.18 Halogenation of Higher Alkanes
From Bond Enthalpies to Heats of Reaction
4.19 Summary
Descriptive Passage and Interpretive Problems 4: More About Potential Energy Diagrams
Chapter 5 - Structure and Preparation of Alkenes: Elimination Reactions
5.1 Alkene Nomenclature
5.2 Structure and Bonding in Alkenes
5.3 Isomerism in Alkenes
5.4 Naming Stereoisomeric Alkenes by the E-Z Notational System
5.5 Physical Properties on Alkenes
5.6 Relative Stabilities of Alkenes
5.7 Cycloalkenes
5.8 Preparations of Alkenes: Elimination Reactions
5.9 Dehydration of Alcohols
5.10 Regioselectivity in Alcohol Dehydration: The Zaitsev Rule
5.11 Stereoselectivity in Alcohol Dehydration
5.12 The E1 and E2 Mechanisms of Alcohol Dehydration
5.13 Rearrangements in Alcohol Dehydration
5.14 Dehydrohalogenation of Alkyl Halides
5.15 The E2 Mechanism of Dehydrohalogenation of Alkyl Halides
5.16 Anti Elimination in E2 Reactions: Stereoelectronic Effects
5.17 Isotope Effects and the E2 Mechanism
5.18 The E1 Mechanism of Dehydrohalogenation of Alkyl Halides
5.19 Summary
Descriptive Passage and Interpretive Problems 5: A Mechanistic Preview of Addition Reactions
Chapter 6 - Reactions of Alkenes
6.1 Hydrogenation of Alkenes
6.2 Heats of Hydrogenation
6.3 Stereochemistry of Alkene Hydrogenation
6.4 Electrophilic Addition of Hydrogen Halides to Alkenes
6.5 Regioselectivity of Hydrogen Halide Addition: Markovnikov's Rule
6.6 Mechanistic Basis for Markovnikov's Rule
Rules, Laws, Theories, and the Scientific Method
6.7 Carbocation Rearrangements in Hydrogen Halide Addition to Alkenes
6.8 Free-Radical Addition of Hydrogen Bromide to Alkenes
6.9 Addition of Sulfuric Acid to Alkenes
6.10 Acid-Catalyzed Hydration of Alkenes
6.11 Thermodynamics of Addition - Elimination Equilibria
6.12 Hydroboration-Oxidation of Alkenes
6.13 Stereochemistry of Hydroboration-Oxidation
6.14 Mechanism of Hydroboration-Oxidation
6.15 Addition of Halogens to Alkenes
6.16 Stereochemistry of Halogen Addition
6.17 Mechanism of Halogen Addition to Alkenes: Halonium Ions
6.18 Conversion of Alkenes to Vicinal Halohydrins
6.19 Epoxidation of Alkenes
6.20 Ozonolysis of Alkenes
6.21 Introduction to Organic Chemical Synthesis
6.22 Reactions of Alkenes with Alkenes: Polymerization
Ethylene and Propane: The Most Important Industrial Organic Chemicals
6.23 Summary
Descriptive Passage and Interpretive Problems 6: Some Unusual Electrophilic Additions
Chapter 7 - Stereochemistry
7.1 Molecular Chirality: Enantiomers
7.2 The Chirality Center
7.3 Symmetry in Achiral Structures
7.4 Optical Activity
7.5 Absolute and Relative Configuration
7.6 The Cahn-Ingold-Prelog R-S Notation System
7.7 Fischer Projections
7.8 Properties of Enantiomers
Chiral Drugs
7.9 Reactions That Create a Chirality Center
7.10 Chiral Molecules With Two Chirality Centers
7.11 Achiral Molecules With Two Chirality Centers
7.12 Molecules With Multiple Chirality Centers
Chirality of Disubstituted Cyclohexanes
7.13 Reactions That Produce Diastereomers
7.14 Resolution of Enantiomers
7.15 Stereoregular Polymers
7.16 Chirality Centers Other Than Carbon
7.17 Summary
Descriptive Passage and Interpretive Problems 7: Prochirality
Chapter 8 - Nucleophilic Substitution
8.1 Functional Group Transformation by Nucleophilic Substitution
8.2 Relative Reactivity of Halide Leaving Groups
8.3 The SN2 Mechanism of Nucleophilic Substitution
8.4 Steric Effects and SN2 Reaction Rates
8.5 Nucleophiles and Nucleophilicity
8.6 The SN1 Mechanism of Nucleophilic Substitution
Enzyme-Catalyzed Nucleophilic Substitution of Alkyl Halides
8.7 Carbocation Stability and SN1 Reaction Rates
8.8 Stereochemistry of SN1 Reactions
8.9 Carbocation Rearrangements in SN1 Reactions
8.10 Effect of Solvent on the Rate of Nucleophilic Substitution
8.11 Substitution and Elimination as Competing Reactions
8.12 Nucleophilic Substitution of Alkyl Sulfonates
8.13 Looking Back: Reactions of Alcohols with Hydrogen Halides
8.14 Summary
Descriptive Passage and Interpretive Problems 8: Nucleophilic Substitution
Chapter 9 - Alkynes
9.1 Sources of Alkynes
9.2 Nomenclature
9.3 Physical Properties of Alkynes
9.4 Structure and Bonding in Alkynes: sp Hybridization
9.5 Acidity of Acetylene and Terminal Alkynes
9.6 Preparation of Alkynes by Alkylation of Acetylene and Terminal Alkynes
9.7 Preparation of Alkynes by Elimination Reactions
9.8 Reactions of Alkynes
9.9 Hydrogenation of Alkynes
9.10 Metal-Ammonia Reduction of Alkynes
9.11 Addition of Hydrogen Halides to Alkynes
9.12 Hydration of Alkynes
9.13 Addition of Halogens to Alkynes
Some Things That Can Be Made From Acetylene...But Aren't
9.14 Ozonolysis of Alkynes
9.15 Summary
Descriptive Passage and Interpretive Problems 9: Thinking Mechanistically About Alkynes
Chapter 10 - Conjugation in alkadienes and Allylic Systems
10.1 The Allyl Group
10.2 Allylic Carbocations
10.3 SN1 Reactions of Allylic Halides
10.4 SN2 Reactions of Allylic Halides
10.5 Allylic Free Radicals
10.6 Allylic Halogenation
10.7 Allylic Anions
10.8 Classes of Dienes
10.9 Relative Stabilities of Dienes
10.10 Bonding in Conjugated Dienes
10.11 Bonding in Allenes
10.12 Preparation of Dienes
10.13 Addition of Hydrogen Halides to Conjugated Dienes
10.14 Halogen Addition to Dienes
10.15 The Diels-Alder Reaction
Dienes Polymers
10.16 The Molecular Orbitals of Ethylene and 1,3-Butadiene
10.17 A Molecular Orbital Analysis of the Diels-Alder Reaction
10.18 Summary
Descriptive Passage and Interpretive Passages 10: Intramolecular and Retro Diels-Alder Reactions
Chapter 11 - Arenes and Aromaticity
11.1 Benzene
11.2 Kekule and the Structure of Benzene
11.3 A Resonance Picture of Bonding in Benzene
11.4 The stability of Benzene
11.5 An Orbital hybridization View of Bonding in Benzene
11.6 The p Molecular Orbitals of Benzene
11.7 Substituted Derivatives of Benzene and their Nomenclature
11.8 Polycyclic Aromatic Hydrocarbons
11.9 Physical Properties of Arenes
Carbon Clusters, Fullerenes, and Nanotubes
11.10 Reactions of Arenes. A Preview.
11.11 The Birch Reduction
11.12 Free-Radical Halogenation of Alkylbenzenes
11.13 Oxidation of Alkylbenzenes
11.14 SN1 Reactions of Benzylic Halides
11.15 SN2 Reactions of Benzylic Halides
11.16 Preparation of Alkenylbenzenes
11.17 Addition Reactions of Alkenylbenzenes
11.18 Polymerization of Styrene
11.19 Cyclobutadiene and Cyclooctatetraene
11.20 Huckel's Rule
11.21 Annulenes
11.22 Aromatic Ions
11.23 Heterocyclic Aromatic Compounds
11.24 Heterocyclic Aromatic Compounds and Huckel's Rule
11.25 Summary
Descriptive Passage and Interpretive Problems 11: The Hammett Equation
CHAPTER 12 - Reactions of Arenes: Electrophilic Aromatic Substitution
12.1 Representative Electrophilic Aromatic Substitution Reactions of Benzene
12.2 Mechanistic Principles of Electrophilic Aromatic Substitution
12.3 Nitration of Benzene
12.4 Sulfonation of Benzene
12.5 Halogenation of Benzene
12.6 Friedel–Crafts Alkylation of Benzene
12.7 Friedel–Crafts Acylation of Benzene
12.8 Synthesis of Alkylbenzenes by Acylation–Reduction
12.9 Rate and Regioselectivity in Electrophilic Aromatic Substitution
12.10 Rate and Regioselectivity in the Nitration of Toluene
12.11 Rate and Regioselectivity in the Nitration of (Trifluoromethyl)benzene
12.12 Substituent Effects in Electrophilic Aromatic Substitution: Activating Substituents
12.13 Substituent Effects in Electrophilic Aromatic Substitution: Strongly Deactivating Substituents
12.14 Substituent Effects in Electrophilic Aromatic Substitution: Halogens
12.15 Multiple Substituent Effects
12.16 Regioselective Synthesis of Disubstituted Aromatic Compounds
12.17 Substitution in Naphthalene
12.18 Substitution in Heterocyclic Aromatic Compounds
12.19 Summary
Descriptive Passage and Interpretive Problems 12: Nucleophilic Aromatic Substitution
CHAPTER 13 - Spectroscopy
13.1 Principles of Molecular Spectroscopy: Electromagnetic Radiation
13.2 Principles of Molecular Spectroscopy: Quantized Energy States
13.3 Introduction to 1 H NMR Spectroscopy
13.4 Nuclear Shielding and 1 H Chemical Shifts
13.5 Effects of Molecular Structure on 1 H Chemical Shifts
Ring Currents—Aromatic and Antiaromatic
13.6 Interpreting 1 H NMR Spectra
13.7 Spin–Spin Splitting in 1 H NMR Spectroscopy
13.8 Splitting Patterns: The Ethyl Group
13.9 Splitting Patterns: The Isopropyl Group
13.10 Splitting Patterns: Pairs of Doublets
13.11 Complex Splitting Patterns
13.12 1 H NMR Spectra of Alcohols
Magnetic Resonance Imaging (MRI)
13.13 NMR and Conformations
13.14 13 C NMR Spectroscopy
13.15 13 C Chemical Shifts
13.16 13 C NMR and Peak Intensities
13.17 13 C 1 H Coupling
13.18 Using DEPT to Count Hydrogens Attached to 13C
13.19 2D NMR: COSY and HETCOR
13.20 Introduction to Infrared Spectroscopy
Spectra by the Thousands
13.21 Infrared Spectra
13.22 Characteristic Absorption Frequencies
13.23 Ultraviolet-Visible (UV-VIS) Spectroscopy
13.24 Mass Spectrometry
13.25 Molecular Formula as a Clue to Structure
Gas Chromatography, GC/MS, and MS/MS
13.26 Summary
Descriptive Passage and Interpretive Problems 13: Calculating Aromatic 13C Chemical Shifts
CHAPTER 14 - Organometallic Compounds
14.1 Organometallic Nomenclature
14.2 Carbon–Metal Bonds in Organometallic Compounds 14.3 Preparation of Organolithium Compounds
14.4 Preparation of Organomagnesium Compounds: Grignard Reagents
14.5 Organolithium and Organomagnesium Compounds as Brønsted Bases
14.6 Synthesis of Alcohols Using Grignard Reagents
14.7 Synthesis of Alcohols Using Organolithium Reagents
14.8 Synthesis of Acetylenic Alcohols
14.9 Retrosynthetic Analysis
14.10 Preparation of Tertiary Alcohols from Esters and Grignard Reagents
14.11 Alkane Synthesis Using Organocopper Reagents
14.12 An Organozinc Reagent for Cyclopropane Synthesis
14.13 Carbenes and Carbenoids
14.14 Transition-Metal Organometallic Compounds
An Organometallic Compound That Occurs Naturally: Coenzyme B12
14.15 Homogeneous Catalytic Hydrogenation
14.16 Olefin Metathesis
14.17 Ziegler–Natta Catalysis of Alkene Polymerization
14.18 Summary
Descriptive Passage and Interpretive Problems 14: Oxymercuration
CHAPTER 15 - Alcohols, Diols, and Thiols
15.1 Sources of Alcohols
15.2 Preparation of Alcohols by Reduction of Aldehydes and Ketones
15.3 Preparation of Alcohols by Reduction of Carboxylic Acids and Esters
15.4 Preparation of Alcohols from Epoxides
15.5 Preparation of Diols
15.6 Reactions of Alcohols: A Review and a Preview
15.7 Conversion of Alcohols to Ethers
15.8 Esterification
15.9 Esters of Inorganic Acids
15.10 Oxidation of Alcohols
15.11 Biological Oxidation of Alcohols
Economic and Environmental Factors in Organic Synthesis
15.12 Oxidative Cleavage of Vicinal Diols
15.13 Thiols
15.14 Spectroscopic Analysis of Alcohols and Thiols
15.15 Summary
Descriptive Passage and Interpretive Problems 15: The Pinacol Rearrangement
CHAPTER 16 - Ethers, Epoxides, and Sulfides
16.1 Nomenclature of Ethers, Epoxides, and Sulfides
16.2 Structure and Bonding in Ethers and Epoxides
16.3 Physical Properties of Ethers
16.4 Crown Ethers
16.5 Preparation of Ethers
Polyether Antibiotics
16.6 The Williamson Ether Synthesis
16.7 Reactions of Ethers: A Review and a Preview
16.8 Acid-Catalyzed Cleavage of Ethers
16.9 Preparation of Epoxides: A Review and a Preview
16.10 Conversion of Vicinal Halohydrins to Epoxides
16.11 Reactions of Epoxides: A Review and a Preview
16.12 Nucleophilic Ring Opening of Epoxides
16.13 Acid-Catalyzed Ring Opening of Epoxides
16.14 Epoxides in Biological Processes
16.15 Preparation of Sulfides
16.16 Oxidation of Sulfides: Sulfoxides and Sulfones
16.17 Alkylation of Sulfides: Sulfonium Salts
16.18 Spectroscopic Analysis of Ethers, Epoxides, and Sulfides
16.19 Summary
Descriptive Passage and Interpretive Problems 16: Epoxide Rearrangements and the NIH Shift
CHAPTER 17 - Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group
17.1 Nomenclature
17.2 Structure and Bonding: The Carbonyl Group
17.3 Physical Properties
17.4 Sources of Aldehydes and Ketones
17.5 Reactions of Aldehydes and Ketones: A Review and a Preview
17.6 Principles of Nucleophilic Addition: Hydration of Aldehydes and Ketones
17.7 Cyanohydrin Formation
17.8 Acetal Formation
17.9 Acetals as Protecting Groups
17.10 Reaction with Primary Amines: Imines
Imines in Biological Chemistry
17.11 Reaction with Secondary Amines: Enamines
17.12 The Wittig Reaction
17.13 Planning an Alkene Synthesis via the Wittig Reaction
17.14 Stereoselective Addition to Carbonyl Groups
17.15 Oxidation of Aldehydes
17.16 Baeyer–Villiger Oxidation of Ketones
17.17 Spectroscopic Analysis of Aldehydes and Ketones
17.18 Summary
Descriptive Passage and Interpretive Problems 17: Alcohols, Aldehydes, and Carbohydrates
CHAPTER 18 - Enols and Enolates
18.1 The -Hydrogen and Its pKa
18.2 The Aldol Condensation
18.3 Mixed Aldol Condensations
18.4 Alkylation of Enolate Ions
18.5 Enolization and Enol Content
18.6 Stabilized Enols
18.7 Halogenation of Aldehydes and Ketones
18.8 Mechanism of Halogenation of Aldehydes and Ketones
18.9 The Haloform Reaction
18.10 Some Chemical and Stereochemical Consequences of Enolization
The Haloform Reaction and the Biosynthesis of Trihalomethanes
18.11 Effects of Conjugation in ,-Unsaturated Aldehydes and Ketones
18.12 Conjugate Addition to ,-Unsaturated Carbonyl Compounds
18.13 Addition of Carbanions to ,-Unsaturated Ketones: The Michael Reaction
18.14 Conjugate Addition of Organocopper Reagents to ,-Unsaturated Carbonyl Compounds
18.15 Summary
Descriptive Passage and Interpretive Problems 18: Enolate Regiochemistry and Stereochemistry
CHAPTER 19 - Carboxylic Acids
19.1 Carboxylic Acid Nomenclature
19.2 Structure and Bonding
19.3 Physical Properties
19.4 Acidity of Carboxylic Acids
19.5 Salts of Carboxylic Acids
19.6 Substituents and Acid Strength
19.7 Ionization of Substituted Benzoic Acids
19.8 Dicarboxylic Acids
19.9 Carbonic Acid
19.10 Sources of Carboxylic Acids
19.11 Synthesis of Carboxylic Acids by the Carboxylation of Grignard Reagents
19.12 Synthesis of Carboxylic Acids by the Preparation and Hydrolysis of Nitriles
19.13 Reactions of Carboxylic Acids: A Review and a Preview
19.14 Mechanism of Acid-Catalyzed Esterification
19.15 Intramolecular Ester Formation: Lactones
19.16 Alpha Halogenation of Carboxylic Acids: The Hell–Volhard–Zelinsky Reaction
19.17 Decarboxylation of Malonic Acid and Related Compounds
19.18 Spectroscopic Analysis of Carboxylic Acids
19.19 Summary
Descriptive Passage and Interpretive Problems 19: Lactonization Methods
CHAPTER 20 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution
20.1 Nomenclature of Carboxylic Acid Derivatives
20.2 Structure and Reactivity of Carboxylic Acid Derivatives
20.3 General Mechanism for Nucleophilic Acyl Substitution
20.4 Nucleophilic Acyl Substitution in Acyl Chlorides
20.5 Nucleophilic Acyl Substitution in Acid Anhydrides
20.6 Sources of Esters
20.7 Physical Properties of Esters
20.8 Reactions of Esters: A Review and a Preview
20.9 Acid-Catalyzed Ester Hydrolysis
20.10 Ester Hydrolysis in Base: Saponification
20.11 Reaction of Esters with Ammonia and Amines
20.12 Amides
20.13 Hydrolysis of Amides
20.14 Lactams
Lactum Antibiotics
20.15 Preparation of Nitriles
20.16 Hydrolysis of Nitriles
20.17 Addition of Grignard Reagents to Nitriles 901
20.18 Spectroscopic Analysis of Carboxylic Acid Derivatives
20.19 Summary
Descriptive Passage and Interpretive Problems 20: Thioesters
CHAPTER 21 - Ester Enolates
21.1 Ester Hydrogens and Their pKa ’s
21.2 The Claisen Condensation
21.3 Intramolecular Claisen Condensation: The Dieckmann Reaction
21.4 Mixed Claisen Condensations
21.5 Acylation of Ketones with Esters
21.6 Ketone Synthesis via -Keto Esters
21.7 The Acetoacetic Ester Synthesis
21.8 The Malonic Ester Synthesis
21.9 Michael Additions of Stabilized Anions
21.10 Reactions of LDA-Generated Ester Enolates
21.11 Summary
Descriptive Passage and Interpretive Problems 21: The Enolate Chemistry of Dianions
CHAPTER 22 - Amines
22.1 Amine Nomenclature
22.2 Structure and Bonding
22.3 Physical Properties
22.4 Basicity of Amines
Amines as Natural Products
22.5 Tetraalkylammonium Salts as Phase-Transfer Catalysts
22.6 Reactions That Lead to Amines: A Review and a Preview
22.7 Preparation of Amines by Alkylation of Ammonia
22.8 The Gabriel Synthesis of Primary Alkylamines
22.9 Preparation of Amines by Reduction
22.10 Reductive Amination
22.11 Reactions of Amines: A Review and a Preview
22.12 Reaction of Amines with Alkyl Halides
22.13 The Hofmann Elimination
22.14 Electrophilic Aromatic Substitution in Arylamines
22.15 Nitrosation of Alkylamines
22.16 Nitrosation of Arylamines
22.17 Synthetic Transformations of Aryl Diazonium Salts
22.18 Azo Coupling
From Dyes to Sulfa Drugs
22.19 Spectroscopic Analysis of Amines
22.20 Summary
Descriptive Passage and Interpretive Problems 22: Synthetic Applications of Enamines
CHAPTER 23 - Aryl Halides
23.1 Bonding in Aryl Halides
23.2 Sources of Aryl Halides
23.3 Physical Properties of Aryl Halides
23.4 Reactions of Aryl Halides: A Review and a Preview
23.5 Nucleophilic Substitution in Nitro-Substituted Aryl Halides
23.6 The Addition–Elimination Mechanism of Nucleophilic Aromatic Substitution
23.7 Related Nucleophilic Aromatic Substitution Reactions
23.8 The Elimination–Addition Mechanism of Nucleophilic Aromatic Substitution: Benzyne
23.9 Diels–Alder Reactions of Benzyne
23.10 m-Benzyne and p-Benzyne
23.11 Summary
Descriptive Passage and Interpretive Problems 23: The Heck Reaction
CHAPTER 24 - Phenols
24.1 Nomenclature
24.2 Structure and Bonding
24.3 Physical Properties
24.4 Acidity of Phenols
24.5 Substituent Effects on the Acidity of Phenols
24.6 Sources of Phenols
24.7 Naturally Occurring Phenols
24.8 Reactions of Phenols: Electrophilic Aromatic Substitution
24.9 Acylation of Phenols
24.10 Carboxylation of Phenols: Aspirin and the Kolbe–Schmitt Reaction
24.11 Preparation of Aryl Ethers
Agent Orange and Dioxin
24.12 Cleavage of Aryl Ethers by Hydrogen Halides
24.13 Claisen Rearrangement of Allyl Aryl Ethers
24.14 Oxidation of Phenols: Quinones
24.15 Spectroscopic Analysis of Phenols
24.16 Summary
Descriptive Passage and Interpretive Problems 24: Directed Metalation of Aryl Ethers
CHAPTER 25 - Carbohydrates
25.1 Classification of Carbohydrates
25.2 Fischer Projections and D–L Notation
25.3 The Aldotetroses
25.4 Aldopentoses and Aldohexoses
25.5 A Mnemonic for Carbohydrate Configurations
25.6 Cyclic Forms of Carbohydrates: Furanose Forms
25.7 Cyclic forms of Carbohydrates: Pyranose Forms
25.8 Mutarotation and the Anomeric Effect
25.9 Ketoses
25.10 Deoxy Sugars
25.11 Amino Sugars
25.12 Branched-Chain Carbohydrates
25.13 Glycosides
25.14 Disaccharides
25.15 Polysaccharides
How Sweet It Is!
25.16 Reactions of Carbohydrates
25.17 Reduction of Monosaccharides
25.18 Oxidation of Monosaccharides
25.19 Cyanohydrin Formation and Chain Extension
25.20 Epimerization, Isomerization, and Retro-Aldol Cleavage
25.21 Acylation and Alkylation of Hydroxyl Groups
25.22 Periodic Acid Oxidation
25.23 Summary
Descriptive Passage and Interpretive Problems 25: Emil Fisher and the structure of (+) - Glucose
CHAPTER 26 - Lipids
26.1 Acetyl Coenzyme A
26.2 Fats, Oils, and Fatty Acids
26.3 Fatty Acid Biosynthesis
26.4 Phospholipids
26.5 Waxes
26.6 Prostaglandins
Nonsteroidal Antiinflammatory Drugs (NSAIDS) and COX-2 Inhibitors
26.7 Terpenes: The Isoprene Rule
26.8 Isopentenyl Diphosphate: The Biological Isoprene Unit
26.9 Carbon–Carbon Bond Formation in Terpene Biosynthesis
26.10 The Pathway from Acetate to Isopentenyl Diphosphate
26.11 Steroids: Cholesterol
26.12 Vitamin D
Good Cholesterol? Bad Cholesterol? What’s the Difference? 26.13 Bile Acids
26.14 Corticosteroids
26.15 Sex Hormones
26.16 Carotenoids
Anabolic Steroids
Crocuses Make Saffron from Carotenes
26.17 Summary
Descriptive Passage and Interpretive Problems 26: Polyketides
CHAPTER 27 - Amino Acids, Peptides, and Proteins
27.1 Classification of Amino Acids
27.2 Stereochemistry of Amino Acids
27.3 Acid–Base Behavior of Amino Acids
27.4 Synthesis of Amino Acids
27.5 Reactions of Amino Acids
27.6 Some Biochemical Reactions of Amino Acids
27.7 Peptides
27.8 Introduction to Peptide Structure Determination
27.9 Amino Acid Analysis
27.10 Partial Hydrolysis of Peptides
27.11 End Group Analysis
27.12 Insulin
27.13 The Edman Degradation and Automated Sequencing of Peptides
Peptide Mapping and MALDI Mass Spectrometry
27.14 The Strategy of Peptide Synthesis
27.15 Amino Group Protection
27.16 Carboxyl Group Protection
27.17 Peptide Bond Formation
27.18 Solid-Phase Peptide Synthesis: The Merrifield Method
27.19 Secondary Structures of Peptides and Proteins
27.20 Tertiary Structure of Polypeptides and Proteins
27.21 Coenzymes
Oh NO! It’s Inorganic!
27.22 Protein Quaternary Structure: Hemoglobin
27.23 Summary
Descriptive Passage and Interpretive Problems 27: Amino Acids in Enantioselective Synthesis
CHAPTER 28 - Nucleosides, Nucleotides, and Nucleic Acids
28.1 Pyrimidines and Purines
28.2 Nucleosides
28.3 Nucleotides
28.4 Bioenergetics
28.5 ATP and Bioenergetics
28.6 Phosphodiesters, Oligonucleotides, and Polynucleotides
28.7 Nucleic Acids
28.8 Secondary Structure of DNA: The Double Helix
“It Has Not Escaped Our Notice . . .”
28.9 Tertiary Structure of DNA: Supercoils
28.10 Replication of DNA
28.11 Ribonucleic Acids
28.12 Protein Biosynthesis
RNA World
28.13 AIDS
28.14 DNA Sequencing
28.15 The Human Genome Project
28.16 DNA Profiling and the Polymerase Chain Reaction
28.17 Summary
Descriptive Passage and Interpretive Problems 28: Oligonucleotide Synthesis
CHAPTER 29 - Synthetic Polymers
29.1 Some Background
29.2 Polymer Nomenclature
29.3 Classification of Polymers: Reaction Type
29.4 Classification of Polymers: Chain-Growth and Step-Growth
29.5 Classification of Polymers: Structure
29.6 Classification of Polymers: Properties
29.7 Addition Polymers: A Review and a Preview
29.8 Chain Branching in Free-Radical Polymerization
29.9 Anionic Polymerization: Living Polymers
29.10 Cationic Polymerization
29.11 Polyamides
29.12 Polyesters
29.13 Polycarbonates
29.14 Polyurethanes
29.15 Copolymers
29.16 Summary
Descriptive Passage and Interpretive Problems 29: Chemical Modification of Polymers

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